D-arabinopyranose

Base Information

• Chemical Name: D-arabinopyranose
• CAS No.: 28697-53-2
• Molecular Formula: C6H8O3
• Molecular Weight: 150.131
• Hs Code.: 29400090
• European Community (EC) Number: 201-767-6,873-441-7
• DSSTox Substance ID: DTXSID101316251
• Nikkaji Number: J766.430C
• Wikidata: Q27120748
• Metabolomics Workbench ID: 56746
• ChEMBL ID: CHEMBL1222249
• Mol file: 28697-53-2.mol

Synonyms:D-arabinopyranose;28697-53-2;(3S,4R,5R)-Tetrahydro-2H-pyran-2,3,4,5-tetraol;(3S,4R,5R)-oxane-2,3,4,5-tetrol;d(-)-arabinose;Arabinose(D);D-?Arabinose;CHEBI:46994;MFCD00064361;50986-18-0;Oxane-2,3,4,5-tetrol, (3S,4R,5R)-;D-(-)-Arabinose, 99%;SCHEMBL112598;CHEMBL1222249;D-(-)-Arabinose, >=98%;D-(-)-Arabinose, 98.5%;DTXSID101316251;87-72-9;HY-N7082;s5134;AKOS016843688;CCG-266200;D-(-)-Arabinose, BioXtra, >=98%;NCGC00165986-01;AS-12470;CS-0030746;A-8200;C00216;EN300-107811;(3S,4R,5R)-Tetrahydropyran-2,3,4,5-tetrol;D-(-)-Arabinose, for microbiology, >=99.0%;O_FULL_00000100000000_GS_790;Q27120748;WURCS=2.0/1,1,0/[a122h-1x_1-5]/1/;Z1255360576;03CC4623-88D1-42C5-8561-3E19735C47D4

Chemical Property of D-arabinopyranose

Chemical Property:

• Appearance/Colour: White to off-white powder
• Vapor Pressure: 9.92E-06mmHg at 25°C
• Melting Point: 162-164 °C(lit.)
• Refractive Index: 1.646
• Boiling Point: 333.2 °C at 760 mmHg
• PKA: 12.26±0.70(Predicted)
• Flash Point: 155.3 °C
• PSA: 90.15000
• Density: 1.757 g/cm³
• LogP: -2.58230
• Storage Temp.: Store at RT.
• Solubility.: H2O: 1 M at 20 °C, clear, colorless
• Water Solubility.: soluble
• XLogP3: -2.5
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 0
• Exact Mass: 150.05282342
• Heavy Atom Count: 10
• Complexity: 117

Purity/Quality:

98%, ^*data from raw suppliers

D-Arabinose ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Biological Agents -> Monosaccharides and Derivatives
• Canonical SMILES: C1C(C(C(C(O1)O)O)O)O
• Isomeric SMILES: C1[C@H]([C@H]([C@@H](C(O1)O)O)O)O
• Uses: An inhibitor of the enzyme glucose dehydrogenase.

Technology Process of D-arabinopyranose

There total 731 articles about D-arabinopyranose which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

chrysoeriol 6-C-anti-α-D-glucopyranoside (89759-25-1) → D-Glucose (2280-44-6) + D-arabinopyranose (28697-53-2) + chrysoeriol (491-71-4)

Guidance literature:

With sulfuric acid; acetic acid; In water; for 10h;

DOI:10.1007/BF00575190

Reference yield:

23,27-dihydroxyoleanolic acid 3-O-β-D-glucopyranosyl(1→4)-α-L-arabinopyranoside → D-glucose (50-99-7) + D-arabinopyranose (28697-53-2)

Guidance literature:

With hydrogenchloride; In water; at 90 ℃; for 6h;

DOI:10.1080/14786419.2019.1634708

Reference yield:

23,27-dihydroxyoleanolic acid 3-O-β-D-glucopyranosyl(1→2)-α-L-arabinopyranoside → D-glucose (50-99-7) + D-arabinopyranose (28697-53-2)

Guidance literature:

With hydrogenchloride; In water; at 90 ℃; for 6h;

DOI:10.1080/14786419.2019.1634708

upstream raw materials:

diazomethane

3-O-β-D-galactopyranosyl-(1->2)-<β-D-xylopyranosyl-(1->3)>-β-D-glucuronopyranosyl quillaic acid 28-O-β-D-apiofuranosyl-(1->3)-β-D-xylopyranosyl-(1->4)-<β-D-glucopyranosyl-(1->3)>-α-L-rhamnopyranosyl-(1->2)-β-D-fucopyranoside.

methanol

D-(+)-xylobiose

Downstream raw materials:

methyl xyloside

methyl-β-D-xylopyranoside

methyl-α-D-xylopyranoside

(2R,3R,4S)-5-[(4,5-Diphenyl-oxazol-2-yl)-hydrazono]-pentane-1,2,3,4-tetraol

Refernces

Glycomimetic building blocks: A divergent synthesis of epimers of shikimic acid

10.1021/ol201252x

The research focuses on the divergent synthesis of (-)-4-epi-shikimic acid, a glycomimetic building block, which is crucial for mimicking carbohydrates and their interactions with C-type lectins (CLECs), proteins involved in physiological and pathological processes. The synthesis route involves a one-pot zinc-mediated reductive ring opening of arabinofuranose, followed by a Barbier reaction and culminating in a ring-closing metathesis. The researchers used D-arabinose as the starting material, converting it to furanose 9 through acid-catalyzed ring contraction, and then to iodosugar 6 using Mitsunobu conditions. The key experiments included optimizing conditions for the Barbier reaction and ring-closing metathesis, with the latter being particularly challenging due to the reactivity of 1,1-disubstituted acrylates. The analyses used to monitor the progress and confirm the structures of the synthesized compounds included NMR and mass spectrometry. The overall yield of the synthetic route was 32%, and the utility of (-)-4-epi-shikimic acid for generating fucose-like compounds was demonstrated through conjugate addition of a thiol, resulting in a product with high diastereoselectivity.

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